Pharmacological Activities and Chemical Stability of Natural and Enzymatically Acylated Anthocyanins: A Comparative Review.

Anthocyanins (ANCs) are naturally occurring water-soluble pigments responsible for conferring red, blue, and purple colors to fruits, vegetables, flowers, and grains. Due to their chemical structure, they are highly susceptible to degradation by external factors, such as pH, light, temperature, and oxygen. Naturally acylated anthocyanins have proven to be more stable in response to external factors and exhibit superior biological effects as compared with their non-acylated analogues. Therefore, synthetic acylation represents a viable alternative to make the application of these compounds more suitable for use. Enzyme-mediated synthetic acylation produces derivatives that are highly similar to those obtained through the natural acylation process, with the main difference between these two pathways being the catalytic site of the enzymes involved in the synthesis; acyltransferases catalyze natural acylation, while lipases catalyze synthetic acylation. In both cases, their active sites perform the addition of carbon chains to the hydroxyl groups of anthocyanin glycosyl moieties. Currently, there is no comparative information regarding natural and enzymatically acylated anthocyanins. In this sense, the aim of this review is to compare natural and enzyme-mediated synthetic acylated anthocyanins in terms of chemical stability and pharmacological activity with a focus on inflammation and diabetes.

Black and pinto beans (Phaseolus vulgaris L.) unique mexican varieties exhibit antioxidant and anti-inflammatory potential.

Oxidative stress and inflammation play a key role in diverse pathological conditions such as cancer and metabolic disorders. The objective of this study was to determine the antioxidant and anti-inflammatory potentials of crude extract (CE) and phenolic-enriched extract (PHE) obtained from the seed coats (SCs) of black bean (BB) and pinto bean (PB) varieties. Delphinidin-3-O-glucoside (46 mg/g SC), malvidin-3-O-glucoside (29.9 mg/g SC), and petunidin-3-O-glucoside (7.5 mg/g SC) were found in major concentrations in the PHE-BB. Pelargonidin (0.53 mg/g SC) was only identified in the PHE-PB. PHE from both varieties showed antioxidant and radical scavenging capacities, with strong correlations associated with total phenolic content (TPC). Polyphenolics, including catechin, myricetin, kaempferol, quercetin, and isorhamnetin glucosides, were identified in the extracts. In terms of the anti-inflammatory potentials, PHE-PB had an IC50 of 10.5 µg dry extract/mL (µg DE/mL) for cyclooxygenase-2 (COX-2) inhibition. The inhibition values for cyclooxygenase-1 (COX-1) ranged from 118.1 to 162.7 µg DE/mL. Regarding inducible nitric oxide synthase (iNOS) inhibition, PHE-BB had an IC50 of 62.6 µg DE/mL. As determined via in silico analysis, pelargonidin showed binding affinities of -7.8 and -8.5 kcal/mol for COX-1 and iNOS, respectively, and catechin had a value of -8.3 kcal/mol for COX-2. Phenolic-enriched extracts from seed coats of black and pinto beans showed good antioxidant and anti-inflammatory potential that warrants in vitro and in vivo studies.

Common beans as a source of food ingredients: Techno-functional and biological potential.

Common beans are an inexpensive source of high-quality food ingredients. They are rich in proteins, slowly digestible starch, fiber, phenolic compounds, and other bioactive molecules that could be separated and processed to obtain value-added ingredients with techno-functional and biological potential. The use of common beans in the food industry is a promising alternative to add nutritional and functional ingredients with a low impact on overall consumer acceptance. Researchers are evaluating traditional and novel technologies to develop functionally enhanced common bean ingredients, such as flours, proteins, starch powders, and phenolic extracts that could be introduced as functional ingredient alternatives in the food industry. This review compiles recent information on processing, techno-functional properties, food applications, and the biological potential of common bean ingredients. The evidence shows that incorporating an adequate proportion of common bean ingredients into regular foods such as pasta, bread, or nutritional bars improves their fiber, protein, phenolic compounds, and glycemic index profile without considerably affecting their organoleptic properties. Additionally, common bean consumption has shown health benefits in the gut microbiome, weight control, and the reduction of the risk of developing noncommunicable diseases. However, food matrix interaction studies and comprehensive clinical trials are needed to develop common bean ingredient applications and validate the health benefits over time.

Black Bean (Phaseolus vulgaris L.) Polyphenolic Extract Exerts Antioxidant and Antiaging Potential.

Phenolic compounds present in common beans (Phaseolus vulgaris L.) have been reported to possess antimicrobial, anti-inflammatory and ultraviolet radiation (UVR) protective properties. UVR from sunlight, which consists of UV-B and UV-A radiations, induces reactive oxygen species (ROS) and free radical formation, consequently activating proteinases and enzymes such as elastase and tyrosinase, leading to premature skin aging. The objective of this work was to extract, characterize and evaluate the antioxidant and antiaging potential of polyphenols from a black bean endemic variety. The polyphenolic extract was obtained from black beans by supercritical fluid extraction (SFE) using CO2 with a mixture of water-ethanol as a cosolvent and conventional leaching with a mixture of water-ethanol as solvent. The polyphenolic extracts were purified and characterized, and antioxidant potential, tyrosinase and elastase inhibitory potentials were measured. The extract obtained using the SFE method using CO2 and H2O-Ethanol (50:50 v/v) as a cosolvent showed the highest total phenolic compounds yield, with 66.60 ± 7.41 mg GAE/g coat (p > 0.05) and 7.30 ± 0.64 mg C3GE/g coat (p < 0.05) of anthocyanins compared to conventional leaching. Nineteen tentative phenolic compounds were identified in leaching crude extract using ESI-QTOF. Quercetin-3-D-galactoside was identified in crude and purified extracts. The purified SFC extract showed IC50 0.05 ± 0.002 and IC50 0.21 ± 0.008 mg/mL for DPPH and ABTS, respectively. The lowest IC50 value of tyrosinase inhibition was 0.143 ± 0.02 mg/mL and 0.005 ± 0.003 mg/mL of elastase inhibition for leaching purified extract. Phenolic compounds presented theoretical free energy values ranging from -5.3 to -7.8 kcal/mol for tyrosinase and -2.5 to -6.8 kcal/mol for elastase in molecular docking (in silico) studies. The results suggest that the purified extracts obtained by SFE or conventional leaching extraction could act as antioxidant and antiaging ingredients for cosmeceutical applications.

Bufadienolides from the Skin Secretions of the Neotropical Toad Rhinella alata (Anura: Bufonidae): Antiprotozoal Activity against Trypanosoma cruzi.

Toads in the family Bufonidae contain bufadienolides in their venom, which are characterized by their chemical diversity and high pharmacological potential. American trypanosomiasis is a neglected disease that affects an estimated 8 million people in tropical and subtropical countries. In this research, we investigated the chemical composition and antitrypanosomal activity of toad venom from Rhinella alata collected in Panama. Structural determination using mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopy led to the identification of 10 bufadienolides. Compounds identified include the following: 16ß-hydroxy-desacetyl-bufotalin-3-adipoyl-arginine ester (1), bufotalin (2), 16ß-hydroxy-desacetyl-bufotalin-3-pimeloyl-arginine ester (3), bufotalin-3-pimeloyl-arginine ester (4), 16ß-hydroxy-desacetyl-bufotalin-3-suberoyl-arginine ester (5), bufotalin-3-suberoyl-arginine ester (6), cinobufagin-3-adipoyl-arginine ester (7), cinobufagin-3-pimeloyl-arginine ester (8), cinobufagin-3-suberoyl-arginine ester (9), and cinobufagin (10). Among these, three new natural products, 1, 3, and 5, are described, and compounds 1-10 are reported for the first time in R. alata. The antitrypanosomal activity assessed in this study revealed that the presence of an arginyl-diacid attached to C-3, and a hydroxyl group at C-14 in the structure of bufadienolides that is important for their biological activity. Bufadienolides showed cytotoxic activity against epithelial kidney Vero cells; however, bufagins (2 and 10) displayed low mammalian cytotoxicity. Compounds 2 and 10 showed activity against the cancer cell lines MCF-7, NCI-H460, and SF-268.

Potential Health Benefits Associated with Lunasin Concentration in Dietary Supplements and Lunasin-Enriched Soy Extract.

Lunasin has demonstrated antioxidative, anti-inflammatory, and chemopreventive properties. The objectives were to evaluate the concentration of lunasin in different lunasin-based commercial dietary supplements, to produce a lunasin-enriched soy extract (LESE) using a two-step pilot-plant-based ultrafiltration process, and to evaluate their biological potential in vitro. LESE was produced using 30 and 1 kDa membranes in a custom-made ultrafiltration skid. Lunasin was quantified in eight products and LESE. Lunasin concentrations of the lunasin-based products ranged from 9.2 ± 0.6 to 25.7 ± 1.1 mg lunasin/g protein. The LESE extract contained 58.2 mg lunasin/g protein, up to 6.3-fold higher lunasin enrichment than lunasin-based dietary supplements. Antioxidant capacity ranged from 121.5 mmol Trolox equivalents (TE)/g in Now® Kids to 354.4 mmol TE/g in LESE. Histone acetyltransferase (HAT) inhibition ranged from 5.3% on Soy Sentials® to 38.3% on synthetic lunasin. ORAC and lunasin concentrations were positively correlated, and HAT and lunasin concentrations were negatively correlated (p < 0.05). Melanoma B16-F10 and A375 cells treated with lunasin showed dose-dependent inhibitory potential (IC50 equivalent to 330 and 370 µM lunasin, respectively). Lunasin showed protein kinase B expression (57 ± 14%) compared to the control (100%) in B16-F10. Lunasin concentration found in commercial products and lunasin-enriched soy extract could exert benefits to consumers.

Food-derived bioactive compounds with anti-aging potential for nutricosmetic and cosmeceutical products.

Besides providing essential nutrients for humans, food contains bioactive compounds that exert diverse biological activities such as anti-microbial, anti-cancerogenic, anti-viral, anti-inflammatory and antioxidant. The cosmetic industry is interested in natural bioactive compounds for their use in nutricosmetic and cosmeceutical products. These products aimed to reduce skin aging, inflammation or provide photoprotection against UV radiation. As a result, nutricosmetics and cosmeceuticals are becoming innovative self-care products in the beauty market. These products contain phytochemicals as active compounds obtained from fruits, vegetables, legumes, medicinal herbs and plants with anti-aging potential. This review summarizes the information within the last 5 years related to bioactive compounds present in fruits, vegetables, herbs and spices commonly used for human consumption. Their antioxidant and biological potential for modulating molecular markers involved in the aging process, as well as their mechanism of action. Diverse natural foods and their byproducts could be used as a source of bioactive compounds for developing cosmeceutical and nutricosmetic products.

Bioactive Compounds, Antioxidant Activity, and Antinutritional Content of Legumes: A Comparison between Four Phaseolus Species.

Beans (Phaseolus spp.) are one of the most important legumes for their nutritional value and health benefits in many world regions. In addition to Phaseolus vulgaris, there are four additional species that are cultivated in many regions of the world and are a source of food for human consumption: P. lunatus, P. coccineus, P. polyanthus, and P. acutifolius. In this work, phenolic compounds, antioxidant activity, and anti-nutritional compounds of 18 bean accessions, corresponding to four different species of the genus Phaseolus, were analyzed. In addition, their physical characteristics, proximate composition, and amino acid content were determined in order to compare their phytochemical composition and nutritional value. The species closest to each other in terms of essential amino acid content were P. polyanthus with P. vulgaris and P. lunatus with P. coccineus. Furthermore, there was a strong positive correlation between antioxidant activity and flavonoids, anthocyanins, and lectins with all the accessions collected. Significant differences in the content of phenolic compounds were found among the bean species studied. Therefore, in addition to P. vulgaris, other species such as P. coccineus and P. lunatus have high biological and antioxidant potential that could be beneficial to human health when consumed as nutraceutical foods.

Black bean peptides inhibit glucose uptake in Caco-2 adenocarcinoma cells by blocking the expression and translocation pathway of glucose transporters.

The objective was to evaluate the effect of black bean protein fraction (PFRA), and its derived peptides on glucose uptake, SGLT1 and GLUT2 expression and translocation on Caco-2 cells. The effect of treatments was evaluated on glucose uptake, protein expression and localization and gene expression on Caco-2 cells. PFRA (10 mg/mL) lowered glucose uptake from 27.4% after 30 min to 33.9% after 180 min of treatment compared to untreated control (p < 0.05). All treatments lowered GLUT2 expression after 30 min of treatment compared to untreated control (31.4 to 48.6%, p < 0.05). Similarly, after 24 h of treatment, GLUT2 was decreased in all treatments (23.5% to 48.9%) (p < 0.05). SGLT1 protein expression decreased 18.3% for LSVSVL (100 µM) to 45.1% for PFRA (10 mg/mL) after 24 h. Immunofluorescence microscopy showed a decrease in expression and membrane translocation of GLUT2 and SGLT1 for all treatments compared to untreated control (p < 0.05). Relative gene expression of SLC2A2 (GLUT2) and SLC5A1 (SGLT1) was downregulated significantly up to two-fold change compared to the untreated control after 24 h treatment. Black bean protein fractions are an inexpensive, functional ingredient with significant biological potential to reduce glucose uptake and could be used as an adjuvant in the treatment of colorectal cancer.

Consumo de jugo de granada (Punica granatum) y su efecto sobre la glucemia, perfil lipídico e histología del páncreas en un modelo de hiperglucemia inducida mediante estreptozotocina / Pomegranate juice consumption (Punica granatum) and its effect on glycemia, lipid profile and histology of the pancreas in a model of induced hyperglycemia by streptozotocin

Diversos compuestos bioactivos de los alimentos se han empleado en el tratamiento alterativo de la diabetes mellitus. El jugo de granada posee un alto contenido en compuestos fenólicos a los cuales se les atribuyen propiedades biológicas como hipolipemiante, hipoglucemiante y protector del tejido pancreático. El objetivo de este estudio fue evaluar el efecto del libre acceso de jugo de granada sobre los niveles de glucosa, colesterol, triglicéridos e integridad del tejido pancreático in vivo. Se emplearon 18 ratas macho Wistar inducidas a hiperglucemia con 60 mg estreptozotocina/kg de peso corporal intraperitoneal (IP). Se formaron tres grupos experimentales. El grupo HS expuesto a solución de sacarosa, el grupo HJG expuesto a jugo de granada y el grupo HSI expuesto a solución de sacarosa y tratamiento con insulina. Los resultados mostraron que, las ratas del grupo HJG consumieron jugo de granada durante 21 días, lo que resultó en la reducción de los niveles de glucosa con respecto a su valor inicial de 417 a 356 mg/dL, no de manera significativa (p>0.05). Los niveles de lípidos mostraron una reducción no significativa al finalizar la intervención (p>0.05). El estudio histológico del páncreas en el grupo HJG mostró conservación de la arquitectura pancreática y presencia de islotes de Langerhans; mientras que el grupo HS mostró extensa necrosis pancreática y el grupo HSI mostró daño intermedio con escasos islotes de Langerhans. Se sugiere que el jugo de granada posee efectos hipoglucemiantes y protege el tejido pancreático en ratas hiperglucémicas inducidas(AU)

Diverse bioactive compounds of foods have been used in the alternative treatment of diabetes mellitus. Pomegranate juice has a high content of phenolic compounds to which biological properties are attributed as lipid-lowering, hypoglycemic and protective of pancreatic tissue. The objective of this study was to evaluate the effect of free access of pomegranate juice on the levels of glucose, cholesterol, triglycerides and the integrity of pancreatic tissue in vivo. Eighteen male Wistar rats were induced to hyperglycemia with 60 mg streptozotocin/kg of body weight intraperitoneal (IP). Three experimental groups were formed. The HS group exposed to sucrose solution, the HJG group exposed to pomegranate juice and the HSI group exposed to sucrose solution and insulin treatment. The results showed that the rats of the HJG group consumed pomegranate juice for 21 days, which resulted in the reduction of glucose levels from its initial value of 417 to 356 mg/dL, not significantly (p>0.05). Lipid levels showed a non-significant reduction at the end of the intervention (p>0.05). The histological study of the pancreas in the HJG group showed conservation of the pancreatic architecture and the presence of islets of Langerhans; while the HS group showed extensive pancreatic necrosis and the HSI group showed intermediate damage with few islets of Langerhans. It is suggested that pomegranate juice has hypoglycaemic effects and protects pancreatic tissue in induced hyperglycemic rats(AU)

Characterization of peptides from common bean protein isolates and their potential to inhibit markers of type-2 diabetes, hypertension and oxidative stress.

BACKGROUND: Diabetes and hypertension are diseases affecting a high proportion of the world population; the use of food-based products such as common bean peptides may contribute to reduce the risk of complications associated to chronic diseases. The aim was to produce and characterize peptides from common bean protein isolates and evaluate their potential to inhibit markers of type-2 diabetes, hypertension and oxidative stress. RESULTS: Mexican black and Brazilian Carioca bean isolated proteins were characterized after pepsin/pancreatin digestion. Also, four synthesized pure peptides, originally found in these beans, were evaluated. Bean protein digests and pure peptides exerted dipeptidyl peptidase-IV (DPP-IV) inhibition (IC50 = 0.03-0.87 mg dry weight (DW) mL-1 ). Lineweaver-Burk plots and computational modeling showed competitive inhibition of DPP-IV. Angiotensin-converting enzyme (ACE) inhibition ranged from IC50 = 0.09 to 0.99 mg DW mL-1 , and α-glucosidase inhibition ranged from 36.3 to 50.1% mg-1 DW. Carioca Perola bean digested proteins presented the highest antioxidant capacity (269.3 mmol L-1 Trolox equivalent g-1 DW) as the peptide KTYGL (P > 0.05) with the most potent DPP-IV and ACE inhibition. CONCLUSION: Peptides from common bean have antidiabetic and antihypertensive potential regardless of their antioxidant capacity. © 2016 Society of Chemical Industry.

Optimization of enzymatic production of anti-diabetic peptides from black bean (Phaseolus vulgaris L.) proteins, their characterization and biological potential.

The aim was to optimize the production of bioactive peptides from black bean (Phaseolus vulgaris L.) protein isolate and to determine their biological potential using biochemical and in silico approaches. Protein fractions were generated using eight commercially available proteases after 2, 3 and 4 h and 1:20, 1:30 and 1:50 enzyme/substrate (E/S) ratios. The best combination of conditions to generate anti-diabetic peptides was with alcalase for 2 h and E/S of 1:20; with inhibition values for dipeptidyl peptidase IV (DPP-IV, 96.7%), α-amylase (53.4%) and α-glucosidase (66.1%). Generated peptides were characterized using LC-ESI-MS/MS. Molecular docking analysis was performed to predict individual peptide biological potential using DockingServer®. Peptides EGLELLLLLLAG, AKSPLF and FEELN inhibited DPP-IV more efficiently in silico through free energy interactions of -9.8, -9.6 and -9.5 kcal mol(-1), respectively, than the control sitagliptin (-8.67 kcal mol(-1)). The peptide TTGGKGGK (-8.97 kcal mol(-1)) had higher inhibitory potential on α-glucosidase compared to the control acarbose (-8.79 kcal mol(-1)). Peptides AKSPLF (-10.2 kcal mol(-1)) and WEVM (-10.1 kcal mol(-1)) generated a lower free energy interaction with the catalytic site of α-amylase in comparison with acarbose (-9.71 kcal mol(-1)). Bean peptides inhibited the tested enzymes through hydrogen bonds, polar and hydrophobic interactions. The main bindings on the catalytic site were with ASP192, GLU192 and ARG 253 on DPP-IV; TYR151, HIS201 and ILE235 on α-amylase; and ASP34, THR83 and ASN32 on α-glucosidase. For the first time, a systematic evaluation and characterization of the anti-diabetic peptides from black bean protein isolate is presented with the potential for inhibiting important molecular markers related to diabetes.

Characterization and Comparison of Protein and Peptide Profiles and their Biological Activities of Improved Common Bean Cultivars (Phaseolus vulgaris L.) from Mexico and Brazil.

Common bean (Phaseolus vulgaris L.) is a good source of protein, vitamins, minerals and complex carbohydrates. The objective was to compare protein profile, including anti-nutrient proteins, and potential bioactive peptides of improved common bean cultivars grown in Mexico and Brazil. Bean protein isolates (BPI) were prepared from 15 common bean cultivars and hydrolyzed using pepsin/pancreatin. Thirteen proteins were identified by SDS-PAGE and protein in-gel tryptic-digestion-LC/MS. Protein profile was similar among common bean cultivars with high concentrations of defense-related proteins. Major identified proteins were phaseolin, lectin, protease and α-amylase inhibitors. Lectin (159.2 to 357.9 mg lectin/g BPI), Kunitz trypsin inhibitor (inh) (4.3 to 75.5 mg trypsin inh/g BPI), Bowman-Birk inhibitor (5.4 to 14.3 µg trypsin-chymotrypsin inh/g BPI) and α-amylase inhibitor activity (2.5 to 14.9% inhibition relative to acarbose/mg BPI) were higher in Mexican beans compared to Brazilian beans. Abundant peptides were identified by HPLC-MS/MS with molecular masses ranging from 300 to 1500 Da and significant sequences were SGAM, DSSG, LLAH, YVAT, EPTE and KPKL. Potential bioactivities of sequenced peptides were angiotensin converting enzyme inhibitor (ACE), dipeptidyl peptidase IV inhibitor (DPP-IV) and antioxidant capacity. Peptides from common bean proteins presented potential biological activities related to control of hypertension and type-2 diabetes.

Impact of commercial precooking of common bean (Phaseolus vulgaris) on the generation of peptides, after pepsin-pancreatin hydrolysis, capable to inhibit dipeptidyl peptidase-IV.

The objective of this research was to determine the bioactive properties of the released peptides from commercially available precook common beans (Phaseolus vulgaris). Bioactive properties and peptide profiles were evaluated in protein hydrolysates of raw and commercially precooked common beans. Five varieties (Black, Pinto, Red, Navy, and Great Northern) were selected for protein extraction, protein and peptide molecular mass profiles, and peptide sequences. Potential bioactivities of hydrolysates, including antioxidant capacity and inhibition of α-amylase, α-glucosidase, dipeptidyl peptidase-IV (DPP-IV), and angiotensin converting enzyme I (ACE) were analyzed after digestion with pepsin/pancreatin. Hydrolysates from Navy beans were the most potent inhibitors of DPP-IV with no statistical differences between precooked and raw (IC50 = 0.093 and 0.095 mg protein/mL, respectively). α-Amylase inhibition was higher for raw Red, Navy and Great Northern beans (36%, 31%, 27% relative to acarbose (rel ac)/mg protein, respectively). α-Glucosidase inhibition among all bean hydrolysates did not show significant differences; however, inhibition values were above 40% rel ac/mg protein. IC50 values for ACE were not significantly different among all bean hydrolysates (range 0.20 to 0.34 mg protein/mL), except for Red bean that presented higher IC50 values. Peptide molecular mass profile ranged from 500 to 3000 Da. A total of 11 and 17 biologically active peptide sequences were identified in raw and precooked beans, respectively. Peptide sequences YAGGS and YAAGS from raw Great Northern and precooked Pinto showed similar amino acid sequences and same potential ACE inhibition activity. Processing did not affect the bioactive properties of released peptides from precooked beans. Commercially precooked beans could contribute to the intake of bioactive peptides and promote health.

Volatile compounds present in traditional meat products (charqui and longaniza sausage) in Chile

The aim of this work was to identify and quantify the volatile compounds in five different commercial brands of charqui and longaniza sausages. Volatile compounds were extracted from some samples headspace using solid phase microextraction (SPME). The identification and quantification were made through the gas chromatography with a mass-selective detector (GS-MS). Fifty-four volatile compounds were identified in charqui samples and thirty-two volatile compounds in longaniza sausages. The chemical groups of the volatile compounds found in both the products were: aldehydes, alcohols, ketones, organic acids, furans, aromatic and aliphatic hydrocarbons. Significant differences were found (p<0.05) in the volatile compounds among the brands of longaniza and charqui. A characteristic volatile compounds profile was not found in the analyzed products. However, an important percentage of the volatile compounds in charqui came from the lipid oxidation. In the case of longanizas sausages, volatile compounds come mainly from the carbohydrates fermentation and spices.